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Generationship

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Episodes (41)

Ep. #56, Vibe Coding for Data with Mark Brocato

Jun 17, 2026 — On episode 56 of Generationship, Rachel Chalmers sits down with Mark Brocato, founder of Mockaroo and creator of Fabricate, to explore the evolution of synthetic data in the age of AI. Mark shares how a simple internal QA tool grew into one of the most...
Ep. #55, Faster Hypothesis Disproving with Sunil Dhaliwal

May 19, 2026 — On episode 55 of Generationship, Rachel Chalmers sits down with Sunil Dhaliwal to explore how AI is reshaping developer infrastructure, venture investing, and computational biology. Sunil reflects on building Amplify Partners during the rise of cloud...
Ep. #54, Human-like Memory with Vishakha Gupta

Apr 21, 2026 — On episode 54 of Generationship, Rachel Chalmers sits down with Vishakha Gupta to explore the hidden infrastructure challenges behind modern AI. They unpack why multimodal data systems are still fragmented, how graph and vector approaches can be...
Ep. #53, The Era of Reimagination with Dr. Mehdi Nourbakhsh

Mar 18, 2026 — On episode 53 of Generationship, Rachel Chalmers sits down with Dr. Mehdi Nourbakhsh to explore how artificial intelligence is transforming the physical and digital worlds. They discuss the origins of generative design, why many AI initiatives fail...
Ep. #52, Serendipity as a Service with Piyush Agarwal

Feb 18, 2026 — On episode 52 of Generationship, Rachel Chalmers sits down with Piyush Agarwal to explore how developer behavior reveals far more about buying intent than traditional sales signals. They discuss why most dev tool GTM strategies fail, how to distinguish...
Ep. #51, AI for Best Practices with Soya Park

Jan 21, 2026 — On episode 51 of Generationship, Rachel Chalmers sits down with Soya Park of Akify to explore why an organization’s most valuable knowledge rarely makes it into formal systems. They discuss how leaders make excellent decisions every day without...
Ep. #50, Defense Against Deepfakes with Joshua McKenty

Dec 22, 2025 — In episode 50 of Generationship, Rachel Chalmers sits down with Joshua McKenty to unpack how AI-driven scams, deepfakes, and identity fraud are already reshaping our digital lives. From scam factories and nation-state actors to broken trust...
Ep. #49, Dumpster Phoenix with Denise Koessler Gosnell and Kathryn Erickson

Dec 10, 2025 — On episode 49 of Generationship, Rachel Chalmers sits down with Denise Koessler Gosnell and Kathryn Erickson to unpack their new book Tech Confidential. Together they explore burnout, leadership, motivation, and the surprising ways our emotional wiring...
Ep. #48, Trusting AI with Sarah Novotny

Nov 26, 2025 — In episode 48 of Generationship, Rachel Chalmers speaks with Sarah Novotny. They dig into why AI models fall short of true creativity, how the tech industry drifted into extractive incentives, and what real security and accountability might look like...
Ep. #47, The Tech Bros with Milette Gillow and Sedinam Simpson

Nov 13, 2025 — In episode 47 of Generationship, Rachel Chalmers chats with Dr. Milette Gillow and Sedinam Simpson, co-founders of The Tech Bros, about their mission to make tech more inclusive and inventive. They unpack lessons from their first accelerator cohort,...